Hydrochloric Acid → (2S,4S)-N-(2-phenylethyl)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide

HRID 1109812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109812
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][C@@H:11]2[CH2:13][C@H:8]1[C:9](=[O:14])[S:10]2)=[O:6])[CH:2]=[CH2:3].[C:15]1([CH2:21][CH2:22][NH2:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>O1CCCC1.C(OCC)(=O)C>[C:15]1([CH2:21][CH2:22][NH:23][C:9]([C@@H:8]2[CH2:13][C@H:11]([SH:10])[CH2:12][N:7]2[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[O:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 15227998(1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one

Produkt 1

HCID 57144107(2S,4S)-N-(2-phenylethyl)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (1S,4S)-5-allyloxycarbonyl-2-thia-5-azabicyclo[2.2.1]heptan-3-one (32.2 mg) in tetrahydrofuran (1 ml) was added 2-phenylethylamine (20.1 mg). The mixture was stirred for 4 hours at room temperature. After the reaction was over, 1N-hydrochloric acid (0.027 ml) was added thereto, and the mixture was diluted with ethyl acetate (2 ml) and dried over magnesium sulfate. Distillation of the solvent, followed by purifying the residue by silica gel chromatography, gave oily (2S,4S) -N-(2-phenylethyl)-1-allyloxycarbonyl-4-mercapto-2-pyrrolidinecarboxamide.

Aufarbeitung

  1. additionwas added
  2. dry with materialdried over magnesium sulfate
  3. distillationDistillation of the solvent
  4. customby purifying the residue by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-969520bccd934c569ba9e585db349b2e
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05322952

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